This Coastal, Cozy Road Trip Highlights Charming Seaside New England Towns And Historic Harbors

The United States is a nation of road trips, from cross-country journeys down Route 66 to winding tours along the scenic and bold Maine coast. And who doesn't love a road trip through New England? While many people might immediately default to autumn drives through the Berkshires, the region's many historic port towns make for a fantastic seaside tour during the spring, summer, or fall.

Port towns are some of the most beautiful and historic settlements in New England. In the days before planes, trains, and automobiles, arriving by sea was the only way to travel. As a result, the oldest parts of town are often around the waterfront. While it may be quicker and easier to arrive by car, these ports offer a glimpse into life as it was hundreds of years ago, while the harbors themselves provide a modern hub for sightseeing cruises, recreational boating, and stunning ocean views.  

This six to nine-day itinerary comes from Darling Travels on Facebook, who notes that it can be adjusted to your taste since the destinations are less than three hours apart. The tour begins in southern New England and moves north toward Maine's rocky shores. The starting point makes it convenient to the major New York area airports or Boston's Logan International, all of which lie about two hours away from the starting point on the Connecticut coast.

This road trip begins in the laidback town of Mystic, Connecticut. Stretched along the shores of the Mystic River, the little village was first settled in 1654. In its early years, it was a hub for shipbuilding and whaling. The must-see 19-acre Mystic Seaport Museum celebrates this history and it's one of the nation's leading maritime museums and one of Connecticut's most visited attractions. The town is also home to the Mystic Aquarium.

The historic area of town stretches along both sides of the river, a walkable area with loads of New England seaside appeal. Olde Mistick Village is an open-air boutique shopping area. Made in the aesthetic of an 18^th-century New England village, it's full of small shops and boutiques.

Heading out of town on either U.S. Highway 1 or Interstate 95, the next stop is one hour east in Newport, Rhode Island. As a quintessential New England summer resort town, lavish mansions and a long-standing yachting tradition are front and center along Narragansett Bay. Don't miss taking a tour of The Breakers, the impressive Gilded Age summer retreat of the Vanderbilt family, or Marble House, another Gilded Age stunner which was used as a setting in the 1970s movie version of "The Great Gatsby."

The next leg of this road trip swings north of Boston to the small town of Salem, roughly two hours north of Newport. The coastal city was made famous by the 1692 witchcraft trials. However, Salem is also one of the original English settlements in the New World with a centuries-long shipbuilding history. As such, it was a base for privateers during both the American Revolution and the War of 1812.

Today, Salem celebrates its history with numerous museums dedicated to the trials and witchcraft in general, ghost tours, and historic buildings loaded with stories and art. There's enough to do in Salem that you might want to dedicate an extra day of your trip just to explore, not to mention the many other port towns in the area you might want to see, such as Marblehead, Gloucester, and Boston.

A little over an hour north on I-95, you'll come to the scenic little town of Ogunquit, Maine. You don't want to miss taking strolls along Perkins Cove, the town's harbor with wharf-side restaurants and shops, or the beautiful Ogunquit Beach. Marginal Way is a cliff-top walking path that connects the two ends of town, offering spectacular ocean views. Ogunquit provides the perfect introduction to the Maine coast: A cozy, welcoming town with plenty of walking, striking views, and several places to try the state's iconic lobster rolls.

Just 20 minutes north on Highway 1 will bring you to Kennebunkport. The town is known for its cute, clapboard town area with art galleries and boutiques, as well as for being the summer vacation destination for President George H.W. Bush and family. For the best shopping, head to the Dock Square area along the harbor. You'll find many restaurants and cafes, boutiques and gift shops, plus art studios and jewelers.

After a 40-minute drive up I-95, you'll arrive in Portland, Maine's largest city and the hub for adventures on Casco Bay. Settled in 1633, the city was built along two rocky headlands overlooking the bay, and it is now an important port. Head to the Old Port district, a walkable historic district of brick buildings and fishing piers. There's a lively food culture with more bar and restaurant options than you can shake a stick at.

There's so much going on in Portland that you might want to plan a full day of exploring. From the port, you can also hop ferries to explore the little islands in Casco Bay, such as idyllic Peaks Island. It's a quiet, residential community with rocky and sandy beaches, stunning Maine coast scenery, and great walking and biking.

Plan to end your New England road trip on Mount Desert Island, home to the charming coastal town of Bar Harbor and one of America's most visited national parks, Acadia. It takes about three hours to drive to Bar Harbor from Portland.

You may want to dedicate one or two days to fully explore all Mount Desert offers, especially if you've never visited before. Bar Harbor is the biggest town on the island, with the most tour, shopping, and food options. If you want to take a whale-watching tour or harbor cruise, it's the best place to look. But you will also want to wander the park's 33 miles of scenic roads and journey over to Northeast and Southwest Harbors on the quiet side of the island. 

Don't miss the drive to the top of Cadillac Mountain, the highest peak on the Eastern Seaboard and the first spot in the country to see sunrise from October through March. There's no shortage of things to do on Mount Desert Island to get you out of your car. If you like to walk or bike ride, the park's 45 miles of carriage roads are worth checking out.

Travel blogger Darling Travels recommended this itinerary as the ultimate bucket list New England road trip aimed at hitting the most charming small-town ports. A definite highlight of each destination is these historic districts' walkable downtowns. And, while each town has its own unique ambiance and feel, each also offers a great variety of places to eat, shop, and stay for the night.

To best experience each destination, maximize your time by finding a hotel right in the heart of the old harbor area. Nearly all these destinations have cozy bed and breakfasts or historic inns that offer a more authentic stay than your average chain hotel. Once there, challenge yourself to park the car and walk everywhere; only use the car when it's time to head for the next destination.

While this trip could be taken any time of year, most tourist-centric towns along the New England coast are seasonal, seeing the most traffic between the Memorial and Labor Day holidays. Remember, the season gets shorter the farther north you travel. But, if you're looking for fall foliage in Acadia or even braving wintery weather for a cozy off-season escape, there's nothing wrong with setting out anytime — outside of major winter storms, of course.